Reaktion #710505

Reaktionsgleichung

Amantadine

1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea

H2O

→

1-(adamantyl)guanidine

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe white precipitate was removed by filtration
2. 2
   WaschenThe precipitate was washed with CH2Cl2 twice
3. 3
   Extraktionthe combined filtrate was extracted with CH2Cl2
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigepurified by flash chromatography
8. 8
   SonstigeThe Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   SonstigeExcess TFA was removed
10. 10
    Sonstigeto give a yellow solid which
11. 11
    Sonstigewas subsequently purified by flash chromatography (0.41 g, 74% over two steps)

Vorschrift

Amantadine (0.30 g, 2 mmol), HgCl2 (0.54 g, 2 mmol), and 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (0.58 g, 2 mmol) were stirred in DMF (10 mL) under a N2 atmosphere for 24 h. H2O was added to the reaction mixture, and the white precipitate was removed by filtration. The precipitate was washed with CH2Cl2 twice, and the combined filtrate was extracted with CH2Cl2, washed with brine and dried over MgSO4, concentrated in vacuo, and purified by flash chromatography. The Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT. Excess TFA was removed by passing N2 through the solution to give a yellow solid which was subsequently purified by flash chromatography (0.41 g, 74% over two steps). 1H-NMR (360 MHz, CD3OD) δ 2.13 (br s, 3H), 1.97 (br s, 6H), 1.76 (br s, 6H); 13C-NMR (90 MHz, CD3OD) δ 160.35, 53.83, 42.45, 36.86, 31.03; ESI-MS: Calculated for C11H19N3 (M+H)+ 194.2. Found: 194.7.

Quelle